Flex Entertainment Lore

Flex Entertainment has had various storylines and events throughout its four year history. This page will contain every significant event.

The Birth of Yung Schmoobin (2017-18)
On August 20, 2017, Simon Orr (aka Yung Schmoobin) uploaded his first song to YouTube, “YouTube Money,” and then uploaded “RisinLikeVerizon,” on December 9, 2017.

The Birth of Lil Flexer (2018)
In February of 2018, Lil Flexer joined Twitter. On March 7, Lil Flexer made his first tweet, that being an announcement for the release of his Ice on my Wrist Music Video. In April, Denzel Brown (aka Lil Mosquito Disease) found out about Lil Flexer on YouTube through his song “Ice On My Wrist” during the time he was still named “Tha Gucci Guy”.

Schmoobin and Big Baller B collide (2018)
Schmoobin discovered Bradley Lehmann through his YouTube channel [Brad Taste in Music] in February 2018. After watching his reaction videos, he found out that Brad made meme rap as well. Schmoobin then reached out to Brad to collab on the YouTube Money Mixtape, which was eventually released in May on Bandcamp. On June 14, Brad released a reaction video to Yung Schmoobin’s YouTube Money Mixtape. Around this time, Adam Barnes, aka A.J., reached out to Schmoobin to work on and share music, and Schmoobin discovered Lil Flexer through TheTopTens.com.

The Birth of Submarine Man (2018)
On May 17, 2018, Submarine Man self released his first EP “Lama Poof” on his BandCamp page. The same year, he met with Lil Flexer to start releasing music under Old Man Dad Records.

Mosquito and Broken Trombone Boi vs. Anime Narrator (2018)
In June of 2018, Mosquito was asked to make a diss track on a man known only by the name "Anime Narrator" by his friend Broken Trombone Boi. After hearing his convincing argument, Brown decided to record a diss with lyrics ghostwritten by Broken Trombone Boi himself.

The song would become known as "Captain Out of Tune" and was released on June 20, 2018. The song was criticized heavily by almost everyone who heard it thanks to the awful single cover which depicted a fish-eye version of a photo of the Anime Narrator provided by Broken Trombone Boi as well as the awful production, lyrics and general nature of the song. The song even made it onto TheTopTens worst songs of 2018 list.

On October 15, Mosquito released his second single "Anime Narrator (Caw Caw)" written by Broken Trombone Boi. Just like “Captain Out of Tune” before it, it received terrible reviews from all audiences.

The Rise of Submarine Man: SESE and NoStockingz (2018)
On August 24, 6ix9ine, Submarine Man, Lama Doodle, and Footye North “released” a song on Spotify called SESE. The song became infamous for its poor production, and its validity is a topic of discussion to this date. Even though the song disappeared a few days later, a couple of people made sure to screen record the song for future reference, and it eventually caused some interest on Submarine Man to grow.

A week later (on August 31,) Submarine Man released his debut album NoStockingz on Old Man Dad Records, which ended up being met with negative reception, although some positive reviews came from rabid Submarine Man stans (which we call Footis,) and not actual music reviewers.

Big Baller B and Lil Mosquito Disease collide (2018)
On November 27. Brad reached out to Lil Mosquito Disease, a rapper that he discovered through TheTopTens.com, on Instagram stating “Is this the real legend himself”. This happened before his Worst Songs of 2018 Video. Mosquito then replied “Yes”.

Lil Meerkat's Weeaboo Paradise (2018)
On November 30, Lil Meerkat dropped a full length mixtape on November 30 called "Weeaboo Paradise Vol. 1" with features from Lil Bodypillow, Lil Mosquito Disease, Tom Sawyer, Submarine Man and many more. The mixtape most notably contains his most popular song, which was a controversial cover of the popular Queen song, “Bohemian Rhapsody.” It was initially received poorly, but then it was recognized as a Flex Entertainment Classic as time went on.

YouTube Money: Reloaded (2018)
On December 10, Brad Taste uploaded his Worst Songs of 2018 videos, and discussed artists like Lil Flexer and Lil Mosquito Disease on the list, bringing new people to their audience, while also introducing the world to Submarine Man and Lil Meerkat. At this time, Schmoobin was already planning on getting a large amount of people to appear on a remix of YouTube Money, and Brad introduced him to just the right group.

On December 11, Brad DMed Mosquito stating “My friend is a soundcloud meme lord. I reviewed one of his projects on my channel. He is trying to get you, and Lil Flexer on a track. I just recorded a verse for the dude. It’s for his “YouTube Money Mixtape 2” It will be Fire. Are you up for it?”. Mosquito then replied “Sure, send me a beat, this boutta be” followed with some fire emojis. Brad then replied “This is gonna be a legendary clashing of gods”. Mosquito then said “Yes”. Brad then said “i’m gonna get the beat from schmoob. Also I shouted you out on my last vid”. Mosquito then said “Ayy”, “You know if flexer gonna be on the track yet, His @ is lilflexerofficial”.

Schmoobin then reached out to all of those artists (excluding Submarine Man) to contribute verses to the eight minute remix of “YouTube Money,”  The track was then released on December 24.

The Birth of Flex Entertainment (2019)
On January 5, Lil Flexer made an announcement on Twitter about the birth of the Flex Entertainment label and how the two labels of Asseating Records and Old Man Dad Records were merged to create it. In the tweet he thanked Yung Schmoobin, Lil Mosquito Disease, Lil Meerkat, A.J., Big Baller B, Submarine Man and two others.

The Rise of Lil Mosquito Disease: Trombone Attacc and Infection (2019)
On January 16, Mosquito released two singles “Trombone Attacc” and “Slide on the Blocc” the latter of which featured Lil Jergens. Trombone Attacc would end up becoming his most popular song and breakout single.

On February 16, Mosquito released his debut studio album "Infection". It was met with mixed to good reviews from audiences and critics, many categorizing it as a great meme rap record. It originally garnered some negative reception from the Horrible Music & Songs Wiki when it first released, but as time progressed, it was then praised as a good meme rap record that succeeded at being comedy. It is considered one of the most iconic Flex albums of all time.

On February 23, Mosquito released his first music video for his song "Trombone Attacc". The video originally ended up gaining 100k views and getting reactions from popular YouTubers like Tommy Craze and Brandon Rashad. The video was praised due to people finding humor in it.

We About To Cause A Swarm (2019)
On March 11, Mosquito released his first collaboration single with Big Baller B “Gang Money”. It was considered one of the biggest Flex flops. On March 22, popular music critic Brad Taste in Music uploaded a video review of Lil Mosquito Disease's "Infection." While he found the first half of the album to be very slow, he praised the second half for making him smile and laugh. He gave the album a 7/10. The next day. Lil Mosquito Disease made his first tweet, which was a retweet of Brad’s review of Infection. After this, both of them began work on a collaboration album titled "Swarm". On March 29, Mosquito and Brad released their single “Feeling Blue” with a feature from the infamous Jaewon XXVI. On July 12, Brad Taste in Music under his stage name Big Baller B and Lil Mosquito Disease released their debut collaboration album titled "Swarm". It received mostly positive reviews from audiences citing the chemistry of the two and the humor for giving them a good laugh. It did have some negative reception from a few people though as well.

The Rise of Tom Sawyer: Daddy (2019)
On March 28, one of the former “artists” on the Flex label, Tom Sawyer, released the now notorious album “Daddy” in a last ditch effort to keep himself in the label, due to the contract stating that an artist is required to release at least 1 album or mixtape a year. Ironically, the album ended up getting a huge amount of backlash due to how unbearable a lot of the material was. For example, in virtually every song on this album, he repeated the song title for the entire song, which showed how severely mundane it was. Another prime example was his vocal editing. His “rapping” (if you can even call it that,) sounded like there were many versions of his voice being overdubbed & layered over on top of each other. Daddy was so awful that even labelmates of Flex Entertainment regret this album being released to this day, and Tom Sawyer ended up being removed from the roster by November.

The Rise of Travis Scotch: The Evolution of Music and Scotchworld (2019-20)
Travis Scotch released his debut single "The Evolution of Music" on August 25, 2019. After multiple delays, Travis Scotch released his project "SCOTCHWORLD" on March 2, 2020. The album gained hundreds of views once again from Brad's review on the project on his channel.

Submarine Man's movie "The Stocking" (2019-20)
On August 31, 2019, the 1 year anniversary of NoStockingz, Submarine Man released a trailer for his movie, The Stocking, under the newly founded movie division of Flex Entertainment, Flex Studios. The movie was announced to be released in the Summer of 2020.

On August 21, 2020, Submarine Man would release his first movie The Stocking onto YouTube. The movie was met with positive reception from Submarine Man’s fans and the Flex community as it was seen as a very funny and grand moment for the Flex community, especially after all the drama during this week.

The Birth of the Flex Entertainment Fan Server (2019)
On October 10, the Flex Entertainment Fan Server was created with the first member being Lil Flexer. The following day (October 11), a YouTube video was put on the label’s channel to invite fans into the server. This marked the beginning of a true golden age, as hundreds of fans could finally directly interact with their favorite Flex artists, and several artists who joined the label would ultimately sign. It spawned a number of memes and elevated the followings of virtually all the artists involved, and truly brought the Flex community together in a way that was never seen before. On February 28, xpstar214 would finally squash his beef with Flex Entertainment, and join their fan server.

AOTY and Flex Entertainment make an agreement (2019)
On October 14, Lil Mosquito Disease & Yung Schmoobin, including reviewers from AlbumOfTheYear like Toasterqueen12, Inglume & thomasny18, as well as the founder of the website, Rob Thomas, signed an official agreement between the website and Flex Entertainment. In the agreement, it resolved the censorship of AOTY user’s music, as artists spamming releases was no longer taking place meaning no need for censorship or confusion.

The Fastoosh Saga (2019-20)
On October 31, the infamous Commander Waterford, better known as Fastoosh Kaloosh joined the Flex Fan Server. He would become a meme legend as almost every sentence he’d type would become a meme on the Flex Entertainment Meme Page on Instagram. Some notable quotes of his include “What is a Aoty? Is it some sort of Dance?”, “Blessed be the Fruit!” and “Lust filled sinner!”. Also on October 31, two future staff members of Flex, Lil Squeaky and Lil Toy Yoda, were signed. On November 11, the infamous Darth Double joined the Flex Fan Server. Around this time Lama Doodle would become active on the server again and would also produce many memes including “Jaewon Maktook”, “I have a big cock” and “I am the college”. On the night of December 9, during a Hunger Games tournament that Schmoobin set up, Lama Doodle secretly listened to the call, and ended up leaking private information (i.e. names and locations,) of some of the Flex Entertainment artists; Mosquito was able to remove the information from the chat quickly.

On January 3, 2020, many Flex Entertainment songs were leaked by an unknown person, although many people on the label felt relieved because only older tracks were leaked. On January 12, the first compilation of Flex Entertainment leaks was placed on SoundCloud. Many people suspect that Fastoosh Kaloosh was behind the leaks due to his face appearing on the album cover, but despite that, the compilation was positively received.

On March 14, another compilation of leaks was released on SoundCloud by an unknown assailant, once again. However this time, it was negatively received due to the person running out of decent material to leak.

Infestation (2019-20)
On November 15, Lil Mosquito Disease released his single “Game of Mosquito” featuring Yung Schmoobin and Submarine Man. It is currently one of his most well received songs. On February 21 2020, Lil Mosquito Disease released his second single for his album Infestation, "33rd Trombone Attacc" with a feature from Big Baller B. On May 14, Lil Mosquito Disease announced that Infestation would be released in one or two weeks. This didn't happen however and it was delayed once again to August. The album ended not meeting the deadlines, which led to Mosquito announcing that the album was complete, but it was slowly being mastered by Kid Phang. To make up for Infestation’s delay, Lil Mosquito Disease announced on July 29 that he would be releasing a new single "Get Shot”, which was released on August 7. The song ended up getting rave reviews, debuted at #7 on the Flex Hot 100 chart, and also got 1K streams on Spotify within a week. On August 25, Lil Mosquito Disease would reveal that his album Infestation was finally complete, and would reveal the tracklist while keeping the names of the features a secret. Amazing Blizzard would also come out and announce that he will be placing a director’s cut version of the album on YouTube a week after Infestation releases. On September 19, Lil Mosquito Disease posted the pre-order link for his highly anticipated album Infestation. It is scheduled to be released on October 9. On October 9, Lil Mosquito Disease releases his highly anticipated album “Infestation”

The Snowfall (2019)
Stemming from the official agreement that AOTY & Flex Entertainment signed a month earlier, they also realized that another reason for the conflict with Flex was the quality of releases coming from the label. Therefore, on November 20, an event that is now known as The Snowfall (named after Low Kii’s “Snowfall Warning”) occurred. This would impact the quality of music that came from the label. Artists who had low commercial success and/or overall terrible music were going to be kicked from the label. The artists being Wild Wes, Footye North, Lama Doodle, Foot Fetish Forever, Lil Hood, Lil PP, lil booty snatcher and Tom Sawyer. The system of contracts was implemented during this time. In hindsight many Flex artists think this was a bad decision with the exclusion of Tom Sawyer’s removal.

The Swift Rise of Beetlebat (2019-20)
Beetle discovered Flex Entertainment through Brad Taste in Music's video about Lil Mosquito Disease's "Infection." He started listening to multiple songs from the label and exploring the Flex Entertainment Worst Music Wiki lore. On November 24, Mosquito tweeted out on his Twitter about the official Flex Entertainment Discord fan server. Beetlebat joined the server around the time of this announcement. On November 25, Mosquito started a Discord server call. Beetle got the courage to finally talk to them. He said “Is this the real Lil Mosquito Disease and Yung Schmoobin?” Throughout the week, he began interacting heavily with the server. He even provided ad libs for Lil Squeaky’s “Menace 2.” He became an active editor of the Flex Entertainment wiki page and Mosquito was taking note. The song was released on November 30, 2019.

Beetle decided to release a song himself, a school project for his Physics class. In October, he was struggling in his physics class so he attempted to do an extra credit activity to boost his grade. One of the options was to create a musical parody that involved physics. He choose his favorite song at the time "Memories" by Maroon 5 as the song to parody. He wrote and recorded the song in an entire day. He showed it to his physics teacher Mr. Mowry, who absolutely loved it. Two months later in December, the teacher showed the song to a group of students who were surprised by the piece. Some students came up to Beetle and convinced him to release it to his YouTube channel along with a music video. He decided to give the people what they want and on December 22, he released "Physics." This was the door that led to a new chapter in his life.

He announced he would be releasing an extended-play titled "Beginnings" in 2020. Mosquito and Schmoobin liked the song and signed him to Flex Entertainment on December 29, 2019. After winter break concluded, Beetle was set on filming a music video for the single in his physics class. He asked Mowry if he could do so during the hour and he accepted. It was recorded in a day and featured him performing the song along with other students. The music video for "Physics" was released on January 12, 2020. The video gained around 200 views in twenty-four hours, a record for him. Maroon 5 themselves may have seen the video. The video currently sits at nearly three thousand views. Mosquito reached out to the Flex community to create a Billboard-like chart for Flex Entertainment singles. Beetle accepted the offer and has been consistently contributing to it for two years.

On January 31, Mosquito and Schmoobin were planning to demote Lil Flexer from Executive, due to how inactive he was (musically and socially.) Possible replacements would be Kid Phang, A.J., and Beetlebat. In the end, Lil Flexer stayed as executive but there was now a fourth executive. Beetlebat was promoted to executive for his dedication to the brand.

The Rise and Fall of Gyfted (2019-20)
On December 5, Lil Mosquito Disease announced that Celine had been signed to Flex Entertainment. MusiklyGyfted was also signed after joining just a few hours earlier, originally as a meme, but later became a serious artist.

On January 20, 2020, Lil Expired Lettuce & MusiklyGyfted (along with MC Icy, beetlebat and Lil French Fries) released a song called “ICU.” Initially upon its release, many considered it to be a Flex anthem, praising the beat, as well as Gyfted & Beetle’s verses. However overtime, the song ended up aging badly.

The very next day, multiple artists were deciding if Gyfted should get kicked off the label. Prior to all of this, he had been the cause of much controversy and stirred up lots of inconsistency and confusion. He has made multiple lies about others on the wiki, aggravated users, and intensified beefs. When Gyfted was being put on the boot list, he responded by guilt tripping people into believing that he had bipolar disorder for sympathy points, but his statement was doubtful. It was also alledged that he sent homophobic slurs and death threats to many people in the past, therefore arousing the tension. His statement was very doubtful to the point where Gyfted in the end was only intensifying the stigma around mentally disorders and got kicked out of the server. Many people has lost their respect on Gyfted, and every last shed of heartfelt sympathy was gone. Later down the road, it was also discovered that he created an intern label without any of the executives’ permission, which was technically a breach in contract. The people signed to his intern label were then transferred to Icy Records.

The Birth of Icy Records and Fall of Wild Wes (2019-20)
On December 15, 2019, Wild Wes was kicked from Flex Entertainment due to choosing quantity over quality, as well as other reasons such as underwhelming critical and commercial success. He went on to co-found the record label Icy Records with MC Icy and EmBee. He was however kicked from that label as well, but he would rejoin Icy Records again a couple months later. On February 7, 2020, after much fighting and beef, Wild Wes finally left the Flex Fan Server due to his inability to take criticism. A couple of weeks after Wild Wes left, he would however return to the server later to apologize for good. He then released a single which showed some improvement compared to his last couple of singles; he was then allowed to rejoin Icy Records.

Flex Entertainment Minecraft Server (2020-22)
See the entire lore storyline at Flex Entertainment Minecraft Server.

Lil Mosquito Disease vs. Knozox (2020)
On January 7, the infamous Knozox released his diss track towards Lil Mosquito Disease simply titled “Lil Mosquito Disease Disstrack”. It featured a rapper called “Extvendy”. It received much negative reception from music reviewers. Amazing Blizzard noticed Knozox’s diss track, and decided to show it to Mosquito, due to how bad the song was.

On January 27, Mosquito released his response to Knozox’s diss track titled “Revenge” after he saw the immense attention that Knozox’s diss on him got. The diss was written in less than an hour. This diss was considered the better of the two by most listeners and has impacted Knozox’s career substantially to the point where most of his videos got more dislikes than likes. Knozox deleted his channel soon after this diss by Mosquito.

The Story of YANG 2012 / GENES1S (2020-21)
On March 15, 1027 was removed from the Flex Entertainment roster due to his projects under YANG 2012 being panned by the audience. Beetlebat said that 1027 had potential as a producer, but his music was forgettable. 1027 had also been criticized for constantly self promoting in Flex Entertainment's Discord server; in fact, his self promotion habits were so constant and irritating that members of the Flex Discord server call people who self promote too much "Yang Criminals" as in his stage name YANG 2012. Two months after he was kicked, he renamed himself as GENES1S.

On June, 24, Flex Entertainment would squash their beef with 1027 (now under the name GENES1S), with Yung Schmoobin unbanning him from their fan server. GENES1S would later be signed by CRZRecords (formally Icy Records).

The Rise of Lil AK Trap (2020)
On March 26, Lil AK Trap released his album “AK’S WORLD 01.” The album received hundreds of plays within a week. It spawned hit singles such as “DOPE” and “COVID-19” which are both huge memes in the Flex community.

Flex Entertainment Hot 100 Controversies (2020-21)
The chart has been subject to a number of controversies during its time. A prominent source of disputes and criticism is the method by which the chart accumulates points; in particular, songs with at least 1,000 streams on Spotify have a massive and unfair advantage over songs that do not, assuming that the artist does not explicitly send Beetlebat the streams for a given song. The chart has also undergone criticism for how the top 10 the same, and very old songs is virtually always still appear on the chart and occupy the top 10 despite their age.

One of the chart’s first number ones would be “Diamond Ores” by Jake G. The song’s popularity occured after it was somehow placed in Sanctuary’s YouTube mix. Thousands of Joji fans discovered the song, which led to it gaining thousands of views every week. Despite there being a lot of dislikes, it still became the third Flex Entertainment song to reach 100K views. Its popularity didn’t die out for months, allowing it to pass “Trombone Attacc” as the most popular Flex song on YouTube at the time.

Perhaps the most infamous controversy came about when Yung Garfield's song "Cosby" took a suspiciously large fall in its second week on the chart, despite its massive second-week numbers on all platforms, including YouTube and SoundCloud, which are much easier to measure. This sparked a massive outcry from Yung Garfield and a number of other artists, who claimed the charts were flawed and that there must have been a miscount. Beetlebat vehemently defended the accuracy of the song's placement on the chart, stating that the second-week numbers were much lower than Garfield thought they were. Beetle addressed this issue, claiming that Garfield had not sent in Spotify numbers that would have assisted its chart position. This controversy sparked Garfield's single "Better Flex Charts," as well as a short-lived plan to develop an entirely different chart system.

Many people believe Beetlebat is biased towards placing Emily Finchum songs high because she is a girl. Almost none of the songs are talked about within the Flex community, but they occupy at least half of the top 10 on many occasions, and her songs have dominated ever since (there has not been another #1 song on the chart since "Bones" went to #1). Fans have called Beetlebat a "simp" for constantly giving Emily higher placements than many believe she deserves, especially considering the poor weekly performance of her songs on Youtube; despite very large view counts, the songs don't accumulate many views in a given week. Beetle addressed this issue by stating that Emily has the highest Spotify numbers in the entire label. "Bones" is said to be getting 10-20K streams a week.

Lil Squeaky's 2018 song "MANNY" had a resurgence in July 2020, and was projected to debut within the top 20, but Beetlebat did not put it on the chart. He claimed the song was too old to chart, and that older songs from Submarine Man and Emily Finchum were allowed to chart because they were "more popular than ever." However, "MANNY" had accumulated far more streams than ever that week, almost quadrupling in SoundCloud streams, and thus it should have charted. Beetlebat owned up to his mistake, and placed it on the chart the next week; however, the resurgence was short-lived, and it dropped off the chart the week after.

Ya Boy Payden was banned from the Flex Entertainment Hot 100 for his first week, due to very high suspicions from numerous people that he was botting his streams. Payden continues to deny that he committed any sort of streaming fraud, but nobody believes him. It is speculated that the massive streams come from one of his friends who had his entire mixtape on loop for a week. Lil AK Trap was also accused of botting and his streams were nerfed.

Beetlebat has received criticism for having an unfair advantage on the charts since he can see all of his streaming numbers on all services and count those towards his chart positions.

Lil Mosquito Disease vs. Jaewon (2020)
On March 24, Jaewon XXVI left Flex Entertainment due to his belief that Flex would ruin his image. After leaving Flex Entertainment however, his career took a downturn as he quit trap music entirely, deleting all of his prior songs to focus on alleged “indie music” that has yet to be released. He has since become a reviled and infamous figure among Flex artists and is often seen as an example of how not to approach making music.

Eat, Sleep, Flex, Repeat: The Quarantine Tape (2020)
On March 27, Yung Schmoobin released his third mixtape “Eat, Sleep, Flex, Repeat.” The project received positive reviews from critics, who called it one of the best meme albums ever. It features songs like “Hippity Hoppity”, “All That”, the title track, and of course “Meningitis.” He was receiving better reviews than major label rappers like Joyner Lucas. At one point, his album was in the top 25 of the year with a rating of 76. Many attribute the organic and random success of this album to have started the trend of Flex Entertainment moving towards pleasing critics instead of making music artists truly liked.

Sites like the Horrible Music & Songs wiki started to take note of Flex Entertainment’s critical improvement. They slowly started to get on their side, realizing that the label isn’t total garbage. Lil Mosquito Disease and Yung Schmoobin were officially added to Best Music Wiki, previously on the Horrible Wiki. Big Baller B will likely join them in the future.

Jessica: The Worst Best Song (2020)
Speaking of Brad, “Jessica” was released by the man. He made the song with the intent of putting together every detail of a bad song. Ironically, it actually got decent reception, and it ended up topping the Flex Entertainment Hot 100 chart, overtaking Jake G's "Diamond Ores,” making “Jessica” become Big Baller B’s first number one single.

Flex Playlist (2020)
Flex Entertainment started branching out to different types of content on their channel. They would host livestreams that invited the viewers to request songs for a Flex Playlist. Other videos include podcasts and compilations. Their first song rating stream was on March 28, but it ended up getting blocked due to Bladee & Yung Lean’s “Gotham City” playing for too long. Amazing Blizzard reuploaded an edited version of the stream to his channel a couple of days after, omitting the clip, while simultaneously adding blurbs.

The Rise of Lil Squeaky (2020)
On April 17, Lil Squeaky released his EP “Squeaky 4 President.” The EP was met with generally positive reviews, with many listeners finding the songs catchy, though others disliked the poor mastering and the very questionable lyrics. The EP spawned Squeaky’s first top ten hit, “Nipples,” which peaked at number 7 on the Flex Entertainment Hot 100. Thanks to this EP and especially the success of "Nipples," Squeaky gained a larger and more dedicated following.

The Deletion of Lil Mosquito Disease and Lil Meerkat's YouTube Channels (2020)
Around the time, Lil Mosquito Disease was still working on Infestation. However on May 1, tragedy struck. Mosquito received an email from YouTube that his YouTube channel had been terminated. Meerkat's channel was also affected. The reason for the termination was the two channels sharing the same email with a reuploads channel that was uploading content against terms of service. He sent an appeal, but YouTube denied it. The original Mosquito channel had over two thousand subscribers and Meerkat was closing in on a thousand. After reaching out to Brad and other members of the Flex community to spread the word, it was clear that his channel was long gone. Mosquito reached out to Beetlebat to create a new YouTube channel and be the new manager of Mosquito's YouTube content. Beetle reuploaded all of Mosquito's music onto the channel on May 3. The reason Mosquito didn't do it himself is the fear that YouTube would terminate the channel again for a previously terminated manager operating it. Meerkat's music would be reuploaded to the Flex Entertainment channel. Since then, Mosquito's channel has reached 1.6K subscribers.

Emily Finchum: The Simp Queen (2020)
On June 17, Emily Finchum, an indie pop artist known for her moody & emotional sound and lyrics (as well as being Kid Floral’s sister,) was signed to Flex Entertainment. The following week, her song “Bones” ended up debuting at number 1 on the Flex Hot 100, due to the song having 100K streams on Spotify, as well as 1M views on YouTube prior to her joining the label, potentially making “Bones” the most popular Flex Entertainment song. Many artists in Flex are said to “simp” for her, and have constantly begged her for features.

The Death of Icy Records (2020)
On June 29, MC Icy was then disowned by the Flex community after it was revealed that he typed out the hard R. It was also discovered that his friends were responsible for botting the scores of his album on AOTY. EmBee would also come out and express his dismay for MC Icy. About 3 days later, MC Icy decided to leave Icy Records after the controversy, and transferred the ownership to CRZFawkz, in which he renamed the label as CRZRecords. But then on August 16, CRZ would then become uninterested, giving the ownership to EmBee, who renamed the label to Billion Dollar Records.

Lil Toy Yoda becomes executive (2020)
On June 30, after a poll made by Mosquito. Lil Toy Yoda would become the fifth executive of Flex Entertainment.

Flex Gang, Volume 2: Dark Ages Show Its Face (2020)
On July 2, the Flex Entertainment label would release the Flex Gang volume 2 compilation, which ended up getting polarizing reviews. Some critics praised the more polished sound of the album compared to many of Flex's previous releases, as well as the improved lyrical content and production, and they praised the last few tracks in particular. "No Words" by Lil Toy Yoda and LVN Filo is considered by many to be one of the greatest songs to come out from the label. However, some critics panned the album for seeming forced and out of character for Flex, and criticized the awkward blend of clearly ironic artists such as Submarine Man with professional sounding artists like Ashi. In hindsight the project has become less celebrated as it for some was the biggest example of what was wrong in the dark ages, in that the label felt compelled to be taken seriously as a legitimate label, while it really was better off as a collective.

God Mode (2020)
On July 24, Lil Squeaky released his second studio album “God Mode.” The album was met with very positive reviews, becoming the highest rated Flex Entertainment album on AOTY. Many listeners and critics praised the more polished sound and improved mixing and mastering, as well as Squeaky's infectious flows and vocal performances and often funny lyrics. Some critics disliked some of the lyrics and mixing, but the majority of listeners gave the album very positive feedback. It is considered among most Flex Entertainment artists and fans to be the best Flex project.

The Rise of Yung Lambo (2020)
On August 6, Yung Lambo released his third single, "Duel of the Fates" featuring Lil Toy Yoda. The song was released with an accompanying music video. The song was met with generally positive reception, with many listeners enjoying how ridiculous the production and lyrics were accompanied by Lambo's deadpan, autotuned delivery and Yoda's very aggressive delivery. Yung Lambo announced his highly anticipated debut album LAMBO SEASON was dropping on October 2.

August 20: The Darkest Day (2020)
On August 19, the biggest and worst drama, known as the “AOTD Drama” officially began. It began after Discord Mod Ava Rose called Lil Squeaky a “bigoted racist” in response to Lil Mosquito Disease stating that Squeaky had helped him with his self confidence issues. Due to this incident Yung Schmoobin, the founder of Flex Entertainment, decided to leave the Flex Discord server. He states that he did due to how stressful it was with “all the constant bickering.”

After this incident, Ava Rose left the server after being demoted from mod due to the rudeness of the incident and a long line of complaints from many Flex artists on how they felt uncomfortable joining calls with them. The drama erupted in other Discord servers as well with Yung Schmoobin appearing to side with Ava Rose. This was met with criticism from the Flex community as they felt betrayed by this.

The next day, Schmoobin was removed from the label, and got demoted from CEO by the exec team due to the bickering and drama he helped cause. Schmoobin alleges that he was NOT kicked and instead left the label due to “background drama” going on. In his statement, he said he would still make music, and that he had made a lot of friends that he still wanted to make music with. At the same time, he took shots at Lil Squeaky for his “far-right political beliefs” and secretly stated he should be banned from the label. The reaction among Flex artists was mixed with some mourning his loss but others feeling mad about the whole drama situation that had begun the day earlier. This drama would continue for weeks on end, being continued onto various other Discord servers including the “AOTD” Discord server. Massive arguments, rumors, and huge amounts of false information were spread, primarily regarding the harmless political views of Lil Squeaky and people calling the label racist and homophobic. Some prominent critics said Squeaky was comparable to an artist who made an album fetishizing rape, and said he was responsible for the deaths of millions and was harming the entire American population. They even called him a “white man,” although he is not. They also said he should get run over by a car, which Schmoobin endorsed. Schmoobin also said he wanted Squeaky booted and banned from the label, and constantly said he had far-right political beliefs and often reaffirmed allegations that he was homophobic and racist.

The reason this drama was the climax of the Dark Ages was that many people feared that these critics would cancel Flex on the AOTY site by leaving misleading reviews with very sensitive allegations, with many statements from the critics alluding to Flex being “cancelled.”  There were moments in which Squeaky considered leaving the label, so that innocent artists who had nothing to do with the situation would not be labeled racists and homophobes. Many people also became very scared that these rumors would cause the most popular and beloved artists, including Big Baller B and Emily Finchum, to leave the label. The situation became toxic to the point that the entire exec and admin teams made several big changes to turn the Flex environment back into somewhere that artists felt safe and free to make the music they liked, not to mention an environment where drama like this wouldn’t occur in the first place. In late August, however, Squeaky asserted that he had done more political research and no longer supported current president Donald Trump in his re-election campaign, which is exactly what triggered the drama where people called him a murderous, homophobic rapist and racist. Despite his apology, some, including Yung Schmoobin, continue to hold toxic views towards the Flex community, and have continued to spread rumors.

BOMBOCLAAT: The End of the Dark Ages
The “Dark Ages” finally came to an end in early September, once Administrator Yung Garfield announced his long-awaited, long-delayed, highly anticipated debut album BOMBOCLAAT.  This album presented a complete contrast to the music that Flex Artists were pressured to make during the Dark Ages, during which they were pressured to make music that would please critics on AOTY. Garfield immediately made it clear that his album would be an unabashed display of his personality, and would not be made to please critics.

Era Four officially began when Flex Entertainment administrator Yung Garfield dropped his highly anticipated debut album BOMBOCLAAT. This era came after what many called the “dark ages” and it felt refreshing that Flex Entertainment artists felt they could make the music they really wanted to make instead of feeling under tremendous pressure from critics. This album was met with love from the Flex community of fans and artists. It was seen as a return to form after the dark ages.

This new era was officially kicked off, and is defined by Flex attempting to regain the magic that it held around a year before upon the creation of the Discord server. The ultimate goal of this era is to strengthen Flex’s sense of community, and stress enjoyment in music and a casual, lighthearted atmosphere. At this point, Flex had officially cut ties with many of the critics from AOTY that they used to work with.

Tending Bike and CRZFawkz Return (2020)
On September 20, Tending Bike and CRZFawkz were both signed to Flex again after improving their sound and becoming more dedicated to their craft. Their return was celebrated by the community. Ben Kenobi was also signed on this day.

5ach!† vs. Lil Squeaky: "Turn It Up" Engineer Battle (2020-21)
Beetle got into a beef with electronic producer 5ach!†. 5ach!† was originally commissioned to mix one of Beetlebat's songs "Turn it Up", but after a decision of banning him from the Flex Entertainment Discord server, he was blocked and fired, with the mixing being handled with Lil Squeaky instead. A few months later after the song's release on "Beginnings", 5ach!† decided to call out to Beetlebat and Lil Squeaky. 5ach!† claimed it was "unfair" due to him being friended with Beetlebat on Discord which made no reason for Beetlebat to block him, as well as his dislike over Lil Squeaky's mix in the song which had vocals (whether intentionally or not) louder than the beat. Their beef was later settled with 5ach!†'s remix of Beetle's song "Sun Goes Down" which was produced by Lil Squeaky.

Beetlebat's Demotion (2020-21)
Beetlebat's promotion to executive in January 2020 sparked much debate about how qualified he was to be an executive, and his lack of contributions sparked much criticism of his position. He was demoted to Admin in November 2020. Beetle took the demotion maturely and accepted he needed to help the label out again. Some say he has helped the label more since being demoted. Beetle explained that he had been taking a month break from the community and the staff team happened to notice his inactivity around that time. He returned to executive status on February 23, 2022, following the label's regret of the decision.

Ashi's Dream Debut Album "Lion" (2020)
On November 13, 2020, Squeaky talked about having a dream where Ashi, one of Flex's only R&B artists known for being extremely distant from the community, announced in the discord server that he wanted to become a lion. He would release his debut album under the name "Lion." He claimed Ashi went into the announcements and atted everyone and saying "Well it's about time I drop something for once lol...I don't care how you guys will take this, but all my life my greatest dream has been to become a lion. That is what I am deep down, and that is what I want to be. Thus, I am proud to announce my debut studio album, Lion. Feel free to contact me if you wanna feature." Squeaky was then added to a group chat made by Ashi, which contained the two of them plus Lil Mosquito Disease and beetlebat. It was said to be released in 2021. Upon Squeaky describing his dream, Lion immediately gained widespread attention from the community. A fake tracklist for the album has since been leaked. Ashi would return to the discord server on November 22, saying that the album wasn't far off from his vision. He hasn't spoken in the Flex server and only released two songs since then so it's likely the album won't see the light of day.

57W1ZARD is Yung Lasagna (2020-21)
In December 2020, it was rumored that 57W1ZARD was Yung Lasagna, a rapper who was previously banned from the server. He ended up being kicked due to the high suspicions from users he was an alt account. In February 2021 it was fully confirmed that 57W1ZARd is in fact Yung Lasagna. He later on left and tried to move away from Flex and started reviving his collective "penis gang" with tongs the following month with Voda Wake rejoining.

A.J. vs Yung Lambo and Yung Garfield (2020-21)
A.J. has gotten in several controversies with Flex Entertainment artists Yung Garfield and Yung Lambo as she banned both of them from her "Neptune" server. She called Yung Garfield "the worst person I've ever met on this app" which received great flack from the Flex community as a rude comment. As of May 2021, A.J. and Yung Lambo have put aside their "beef" and now Yung Lambo streams Rose Gold on repeat on Spotify. Garfield and A.J. have yet to reconcile.

The Story of "Sun Goes Down" (2021)
Lil Squeaky reached out to Beetlebat, telling him he should make an EDM song. This statement got the attention of many people in the Flex Discord Server, becoming a short lived copy pasta. Squeaky sent him a tropical house instrumental to use and Beetle worked on it for about a month. He asked his friend Ben Riggle to hop on the track as he was a big fan of electronic house music. Beetle announced the track on March 26, 2021. It was released a day later. A remix was later made by Canadian producer 5ach!† and was released on May 28th and received mixed reviews. A music video originally wasn’t planned to happen but it ended up being considered after they decided to meet up in Indianapolis. Beetle and Riggle met up in Indianapolis on June 30 to film a music video for the single. The music video was filmed at an Indianapolis Marriott Downtown hotel. It features Beetle and Riggle performing the song at various places like their room, garden, and lake. It is a vlog style visual where the two artists hold the camera themselves. It was finally released on July 9. It was praised by the Flex community, cementing itself as Flex’s song of the summer.

Beetlebat's Rumored Debut Album: The Middle (2021)
Beetlebat was highly speculated to release an album called "The Middle" in 2021 after former Flex Entertainment artist Lil Squeaky revealed a "tracklist" for the project. The tracklist featured appearances from a wide variety of artists from Canadian Prime Minister Justin Trudeau to former Flex Entertainment artist Amazing Blizzard. Beetle confirmed the album was not happening.